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I’ve long wanted to write something about maocrystal V total synthesis, but I’ve always been too busy around the time that people have completed it to get a blog post out reasonably close to the event. Fortunately, two back-to-back syntheses from the Zakarian and Thomson groups were published in J. Am. Chem. Soc. earlier this month and I’ve now got plenty time to write about both of them, starting with that of the Thomson group in this post.

Synthesis of cephalosporin-4-aldehydes.

T1 - Penicillin-cephalosporin conversion. VII. An improved synthesis of 3-methylenecephams

Synthesis and chemistry of cephalosporin ..

This week’s group meeting’s talk on ‘Strategies in Synthetic Planning’ raised a number of interesting points for discussion, but I wanted to put just one to my readers and the online synthetic community: what’s your favourite total synthesis?


Paul Dochety's blog at was a massive inspiration to me in my early days as a blogger, showing me that there was enough of a synthetic organic chemistry community online to make writing seemingly very esoteric posts on a small, specialised sub-field rewarding and worthwhile. A couple of years ago, Paul moved away from the online community, but continued his excellent monthly column for the RSC's (think British C&EN, if you're not familiar with it). However, his tenure there has recently also , and to try to fill the organic-shaped hole in its opinion pages the RSC has commisioned a new column – Organic Matter. As you've probably , authorship will be shared between myself, Karl Collins (of ) and the legendary Chemjobber (anyone who needs a should really rethink their blog-reading priorities).

B.R.S.M. — A blog about total synthesis, organic synthesis and chemical history

Synthesis of a cephalosporin-doxorubicin antitumor ..

Given the massive number of people affected worldwide by neurodegenerative diseases and nerve injuries, it's not surprising that a number of synthetic groups have chosen to focus their research programs on neurotrophic[1] natural products. Of course, it's probably coincidence that aside from their potential uses to society, a number of these compounds seem to also be structurally unique and strikingly intricate molecules.[2] One such example is jiadifenolide, whose dense, caged seco-prezizaane-type structure has already seen 3 total syntheses since its isolation five years ago.

Synthesis Of Dipeptide Linked-cephalosporins To …

In the four months I spent not writing this post, the Paterson–Dalby synthesis of jiadifenolide was , but as I’d already put a few hours into it I decided to use the Christmas holidays to dust it off and finish it up. Enjoy! —BRSM

Synthesis of a cephalosporin analogue

Cephalosporins/chemical synthesis* Cephalosporins/pharmacology;

Sharp eyed readers will note that a large part of this synthesis is adapted from the Zakarian group's previously reported total synthesis of racemic maoecrystal V from back in 2013, and in fact it reuses the same intramolecular Diels–Alder key step to construct the fused furanobicyclo[2.2.2]octane ring system:

Synthesis and preliminary cytotoxicity study of a cephalosporin-CC ..

Design and synthesis of a cephalosporin-carboplatinum prodrug ..

Maoecrystal V—as the advanced nature of its final letter implies—is one of a great many unusual terpinoids from the Chinese flowing plant Isodon eriocalyx.[1] It possesses a rather intricate and complex structure, a fact illustrated by the two decades that passed between its (first) isolation in 1994 and the successful determination of its structure in 2004—a long period indeed with modern spectroscopic techniques. Its dense, cage-like structure proved a tough nut to crack and another 5 years passed before the deluge of synthetic publications for this target began in 2009. The first total synthesis, reported somewhat controversially by the Yang group the following year, has only seemingly intensified the attention that it has received.

Lack of knowledge of the exact chemical structure of cephalosporin antigenic ..

characterization and immunochemical evaluation of cephalosporin ..

I'd initially planned to write about the most recent 2 (or possibly all 3) syntheses in an epic all-in-one comparison blog-post, but in the interests of keeping these musings short and somewhat readable I've decided to break things down a bit. This week's installment will cover Sorenson's awesome synthesis from back in April.